Over time, and depending on the load both the three point hitch and the loader may leak down. It's considered acceptable within certain parameters. JD has published leakdown rates for the loaders that are considered 'in spec', but I haven't seen such for the three point.

When my 1026R started doing that I took it to Deere dealer. They found a small amount of rust on an internal valve and a large score on the internal lift cylinder for the 3 point. I have a thread on it someplace.

If I put mine away with the oil very warm from mowing it will leak down.. If I just run the tractor for a few minutes, mine stays up all the way with my hitch on it.

I figured the viscosity of the hyguard thins out enough when it is hot that it leaks down faster and must leak down all the way before the oil cools, but cold it doesnt leak down hardly at all. Any opinons on if I should take it to get checked out? I was blaming the low vis hyguard lol.

Mine did not leak down no matter how much I used it. Then it got the crud in it and had to be replaced. My tractor can sit for a week between mowing and I know my hitch doesn't move when I start it up. Seems like it should at least be checked out. If you call your dealer they can tell you how much leak down is acceptable with JD.